A short and efficient stereoselective synthesis of all four diastereomers of sphingosine

Practical syntheses of all four stereomers of sphingosine from serine have been achieved through highly diastereoselective reduction of the N-trityl protected alpha'-amino enone derivative 5 with NaBH4 and reduction of the free alpha'-amino enone derivative 7 with Zn(BH4)(2). (C) 2002 Elsevier Science Ltd. All rights reserved.